Transportation is crucial in the delivery of medicines and medical equipment world over. In Africa, the challenge of poor road infrastructure and limited options of delivery channels restrict delivery to road transportation. In Zambia, the Zambia Medicines, and Medical Supplies Agency (ZAMMSA), faces these challenges to deliver medicine to the Last Mile. It would be useful to know how exactly ZAMMSA has responded to the logistical challenges that relate to last mile system. Therefore, the main objective for this research was to evaluate the last mile delivery logistics process performance at ZAMMSA, to investigate challenges of the transportation system in use in relation the Last Mile delivery process, to assess the Last Mile delivery performance at ZAMMSA and to address any challenges pertinent to transportation.  A quantitative approach was used, and data was collected using semi-structured questionnaires. Purposive sampling technique was adopted and 50 employees from ZAMMSA were selected. The data was presented through tables, graphs and charts and standard deviation was used to analyse the responses. Data was analysed using Microsoft excel.  The main findings of the research were that ZAMMSA uses a combined transportation system of own and outsourced vehicles and the challenges of the Last Mile system at ZAMMSA lead to operational inefficiencies. The implication of these results is that the Last Mile logistics system is particularly ideal for organisations that pursue the profit-making objective. However, the Last Mile system can still be used by any logistics Organisation to improve efficiency in the Supply Chain. To improve efficiency and the operation of the Last Mile system at ZAMMSA, it was recommended that staff be trained to understand how the concept is operationalized.